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Seven Seas Grandeur
Regent Seven Seas Cruises
Dec 19, 2026 - Dec 29, 2026 (10 Nights)
Miami • St. Thomas • St John's, Antigua • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$11,799pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Celebrity Eclipse
Celebrity Cruises
Dec 14, 2027 - Dec 23, 2027 (9 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$860pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Mar 17, 2027 - Mar 27, 2027 (10 Nights)
Fort Lauderdale • Grand Turk • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,024pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Rhapsody of the Seas
Royal Caribbean
Dec 18, 2027 - Dec 24, 2027 (6 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Basseterre, St. Kitts and Nevis • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$767pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Scarlet Lady
Virgin Voyages
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$1,164pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Norwegian Bliss
Norwegian Cruise Line
Jan 3, 2028 - Jan 15, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • Tortola • St. Thomas • Manhattan
Average Starting Price
$1,419pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Nov 18, 2026 - Nov 28, 2026 (10 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • Dominica • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$599pp
Jim's Onboard Credit
Adventure of the Seas
Royal Caribbean
Nov 7, 2026 - Nov 15, 2026 (8 Nights)
Fort Lauderdale • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$407pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Eurodam
Holland America Line
Dec 22, 2027 - Jan 12, 2028 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale • Relaxaway Half Moon Cay • Montego Bay, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$5,259pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Star Pride
Windstar Cruises
Nov 15, 2027 - Nov 29, 2027 (14 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Nov 15, 2026 - Nov 25, 2026 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami
Average Starting Price
$2,350pp
Jim's Onboard Credit
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